Chemistry of 2-Amino-3-cyanopyridines

REFERENCES

• Shi , F. ; Tu , S. ; Fang , F. ; Li , T. One-pot synthesis of 2-amino-3-cyanopyridine derivatives under microwave irradiation without solvent . Arkivoc 2005 , 1 , 137 – 142 .
   Web of Science ®Google Scholar
• Ladani , N. K. ; Patel , M. P. ; Patel , R. G. An efficient three-component one-pot synthesis of some new octahydroquinazolinone derivatives and investigation of their antimicrobial activities . Arkivoc 2009 , 7 , 292 .
   Web of Science ®Google Scholar
• Mungra , D. C. ; Patel , M. P. ; Patel , R. G. An efficient one-pot synthesis and vitro antimicrobial activity of new pyridine derivatives bearing the tetrazoloquinoline nucleus . Arkivoc 2009 , 14 , 64 – 74 .
   Google Scholar
• Murata , T. ; Shimada , M. ; Sakakibara , S. ; Yoshino , T. ; Kadono , H. ; Masuda , T. ; Shimazaki , M. ; Shinyani , T. ; Fuchikami , K. ; Sakai , H. I. ; Inbe , H. ; Takeshita , K. ; Niki , T. ; Umeda , M. ; Bacon , K. B. ; Ziegelbauer , K. B. ; Lowinger , T. B. Discovery of novel and selective IKK-β serine-threonine protein kinase inhibitors, part 1 . Bioorg. Med. Chem. Lett. 2003 , 13 , 913 – 918 .
   PubMed Web of Science ®Google Scholar
• Bekhit , A. A. ; Baraka , A. M. Novel milrinone analogs of pyridine-3-carbonitrile derivatives as promising cardiotinic agents . Eur. J. Med. Chem. 2005 , 40 , 1405 – 1413 .
   PubMed Web of Science ®Google Scholar
• Abadi , A. H. ; Abouel-Ella , D. A. ; Lehmann , J. ; Tinsley , H. N. ; Gary , B. D. ; Pizza , G. A. ; Abdel-Fattah , M. A. O. Discovery of colon tumer cell growth inhibitory agents through a combinatorial approach . Eur. J. Med. Chem. 2010 , 45 , 90 – 97 .
   PubMed Web of Science ®Google Scholar
• Oner , R. R. ; Sinha , S. ; Kumar , S. ; Nandi , C. K. ; Ghosh , S. 2-Aminopyridine derivative as fluorescence “on-off” molecular switch for selective detection of Fe3+/Hg2+ . Tetrahedron Lett. 2012 , 53 , 2302 – 2307 .
   Web of Science ®Google Scholar
• Zhang , F. ; Zhao , Y. ; Sun , L. ; Ding , L. ; Gu , Y. ; Gong , P. Synthesis and anti-tumor activity of 2-amino-3-cyano-6-(1H-iindol-3-yl)-4-phenylpyridine derivatives in vitro . Eur. J. Med. Chem. 2011 , 46 , 3149 – 3157 .
   PubMed Web of Science ®Google Scholar
• Khaksar , S. ; Yaghoobi , M. A. Concie and versatile synthesis of 2-amino-3-cyanopyridine derivatives in 2,2,2-trifuroethanol . J. Fluorine Chem. 2012 , 142 , 41 – 44 .
   Web of Science ®Google Scholar
• Shintani , T. ; Kadono , H. ; Kikuchi , T. ; Schubert , T. ; Shogase , Y. ; Shimazaki , M. Efficient synthesis of 3-cyano-6-(2-hydroxyphenyl)pyridines by multi-component condensation on beads . Tetrahedron lett. 2003 , 44 , 6567 – 6569 .
   Web of Science ®Google Scholar
• Zhou , J. F. ; Gong , G. X. ; Zhu , F. X. ; Zhi , S. J. Microwave-promoted one-pot synthesis of 3-(2′-amino-3′-cyano-4′-arylpyrid-6′-yl) coumarins . Chin. Chem. Lett. 2009 , 20 , 37 – 39 .
   Web of Science ®Google Scholar
• Tang , J. ; Wang , L. ; Yao , Y. ; Zhang , L. ; Wang , W. One-pot synthesis of 2-amino-3-cyanopyridine derivatives catalyzed by ytterbium perflurooctanoate [Yb(PFO)3] . Tetrahedron Lett. 2011 , 52 , 509 – 511 .
   Web of Science ®Google Scholar
• Shibani , H. ; Saidi , K. ; Abbasnejad , M. ; Derakhani , A. A convenient one-pot synthesis and anxietic activity of 3-cyano-2(1H)-iminopyridines and halogen derivatives of benzo[h]chromenes . Arab. J. Chem. In press .
   Web of Science ®Google Scholar
• Mansoor , S. S. ; Aswin , K. ; Logaiya , K. ; Sudhan , S. P. N. [Bmim]BF4 ionic liquid: An efficient reaction medium for the one-pot multicomponent synthesis of 2-amino-4,6-diphenylpyridine-3-carbonitrile derivatives . J. Saudi Chem. Soc. In press .
   Google Scholar
• Chandrashekhar , C. H. ; Latha , K. P. ; Vagdevi , H. N. ; Vaidya , V. P. One-pot synthesis of 2-amino4-(substituted phenyl)-6-naphtho[2,1-b]furan-2-ylnicotinonitrile derivatives by using bismuth nitrate pentahydrate as efficient catalyst . Pharm. Sinica 2013 , 4 , 37 – 39 .
   Google Scholar
• Pal , S. ; Singh , V. ; Das , P. ; Choudhury , L. H. PEG-mediated one-pot multicomponent reaction for the efficient synthesis of functionalzed dihydropyridines and their functional group dependent DNA cleavage activity. Bioorg. Chem. 2013, 4, 8–15.
   Web of Science ®Google Scholar
• Makawana , J. A. ; Patel , M. P. ; Patel , R. G. Synthesis and in virto antimicrobial evaluation of pentasubstituted pyridine derivatives bearing the quinoline nucleus . Med. Chem. Res. 2012 , 21 , 616 – 623 .
   Web of Science ®Google Scholar
• Banerjee , S. ; Sereda , G. One-step, three-component synthesis of high substituted pyridines using silica nanopartical as reusable catalyst . Tetrahedron Lett. 2009 , 50 , 6959 – 6962 .
   Web of Science ®Google Scholar
• Shi , F. ; Li , C. ; Xia , M. ; Miao , K. ; Zhao , Y. ; Tu , S. ; Zheng , W. ; Zhang , G. ; Ma , N. Green chemoselective synthesis of thiazolo[3,2-a]pyridine derivatives and evaluation of their antioxidant and cytotoxicactivities . Bioorg. Med. Chem. Lett. 2009 , 19 , 5565 – 5568 .
   PubMed Web of Science ®Google Scholar
• Wen , L.-R. ; Jiang , C.-Y. ; Li , M. ; Wang , L.-J. Application of 2-(2-chloroaroyl)methyleneimidazolidines in domino and multicomponent reaction: New entries to imidazo[1,2-a]pyridines and benzo[b]imidazo[1,2,3-ij][1,8]naphtyridines . Tetrahedron 2011 , 67 , 293 – 302 .
   Web of Science ®Google Scholar
• Sakurai , A. ; Midorikawa , H. The cyclization of malononitrile and ketones by ammonium acetate . Bull. Chem. Soc. Japan 1968 , 41 , 430 – 432 .
   Web of Science ®Google Scholar
• Mantri , M. ; de Graaf , O. ; Veldhoven , J. V. ; Göblyös , A. ; Künzel , J. K. F. D. ; Künzel Mulder-Krieger , T. ; Link , R. ; de Vries , H. ; Beukers , M. W. ; Brussee , J. ; Ijzerman , A. P. 2-Amino-6-furan-2-yl-4-substituted nicotinonitrile as A2A adenosine receptor antagonists . J. Med. Chem. 2008 , 51 , 4449 – 4455 .
   PubMed Web of Science ®Google Scholar
• Fuentes , L. ; Lorente , A. ; Soto , J. Synthesis of heterocyclic compounds XIII: 2-Amino-3-benzyl-3,5-dicyano-6-methoxy-4-phenyl-3,4-dihydropyridi-nes . J. Heterocycl. Chem. 1978 , 16 , 273 – 276 .
   Web of Science ®Google Scholar
• El-Gazzar , A.-R. B. A. ; Hafez , H. N. Synthesis of 4-substituted pyrido[2,3-d]pyrimidin-4-(1H)-one as analgesic and anti-inflammatory agent . Bioorg. Med. Chem. Lett. 2009 , 19 , 3392 – 3397 .
   PubMed Web of Science ®Google Scholar
• Hammouda , M. ; Mashaly , M. M. ; Afsah , E. M. Enamines in heterocyclic synthesis: One-pot synthesis of some new quinoline derivatives . Pharmazie 1994 , 49 , 365 – 366 .
   Web of Science ®Google Scholar
• Ghorab , M. M. ; Ragab , F. A. ; Heiba , H. I. ; Arafa , R. K. ; El-Hossary , E. M. Docking study, in vitro anticancer screening and radiosensitizing evaluation of some new fluorine-containing quinoline and pyrimidoquinoline derivatives bearing a sulfonamide moiety . Med. Chem. Res. 2011 , 20 , 388 – 400 .
   Web of Science ®Google Scholar
• Al-Said , M. S. ; Ghorab , M. ; Al-Dosari , M. ; Hamed , M. M. Synthesis and in vitro anticancer evaluation of some novel hexhydroquinoline derivatives having a benzenesulfonamide moiety . Eur. J. Med. Chem. 2011 , 46 , 201 – 207 .
   PubMed Web of Science ®Google Scholar
• Alqasoumi , S. I. ; Al-Taweel , A. M. ; Alafeefy , A. M. ; Noaman , E. ; Ghorab , M. M. Novel quinolines and pyrimido[4,5-b]quinolines bearing biological active sulfonamide moiety as new class of antitumor agents . Eur. J. Med. Chem. 2010 , 45 , 738 – 744 .
   PubMed Web of Science ®Google Scholar
• Gholap , A. R. ; Toti , K. S. ; Shirazi , F. ; Kumari , R. ; Bhat , M. K. ; Deshpande , M. V. ; Srinivasan , K. V. Synthesis and evaluation of antifungal properties of the novel 2-amino-5-oxo–4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile and its analogues . Bioorg. Med. Chem. 2007 , 15 , 6705 – 6715 .
   PubMed Web of Science ®Google Scholar
• Altundas , A. ; Ayvaz , S. ; Logogla , E. Synthesis and evaluation of series of aminocyanopyridines as antimicrobial agent . Med. Chem. Res. 2011 , 20 , 1 – 8 .
   Web of Science ®Google Scholar
• Hammouda , M. ; Abou Zeid , Z. M. ; Metwally , M. A. New simple and one-pot synthesis routes to polyfunctionally substituted imidazo[1,2-a]pyridines, pyrido[1,2-a]pyrimidines, pyrido[1,2-a]-1,3-diazepines, and imidazo[1,2-a]pyrimidines . Chem. Heterocycl. Comp. 2005 , 41 , 1525 – 1528 .
   Google Scholar
• Paul , S. ; Gupta , R. ; Loupy , A. Improved synthesis of 2-amino-3-cyanopyridines in solvent-free conditions under microwave irradiation. J. Chem. Res., Synop. 1998, 330–331.
   Web of Science ®Google Scholar
• Manna , F. ; Chimenti , F. ; Bolasco , A. ; Filippelli , A. ; Palla , A. ; Filippelli , W. ; Lampa , E. ; Mercantini , R. Anti-inflamatory, analgesic, and antipyretic 4,6-disubstituted 3-cyanopyridine-2-ones and 3-cyano-2-aminopyridines . Eur. J. Med. Chem. 1992 , 27 , 627 – 632 .
   Web of Science ®Google Scholar
• Manna , F. ; Chimenti , F. ; Bolasco , A. ; Bizzarri , B. ; Filippelli , W. ; Filippelli , A. ; Gagliardi , L. Anti-inflammatory, analgesic, and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines . Eur. J. Med. Chem. 1999 , 34 , 245 – 254 .
   Web of Science ®Google Scholar
• Vyas , D. H. ; Tala , S. D. ; Akbar , J. D. ; Dhaduk , M. F. ; Joshi , K. A. ; Joshi , H. S. Synthesis and antimicrobial activity of some new cyanopyridine and cyanopyrans towards Mycobacterium tuberculosis and other microorganisms . Indian J. Chem. 2009 , 48 , 833 – 839 .
   Google Scholar
• Konda , S. G. ; Khedkar , V. T. ; Dawane , B. S. Synthesis of some new 2-amino-3-cyano-4-aryl-6-(1-naphthylamino)-pyridines as antibacterial agent . J. Chem. Pharm. Res. 2010 , 2 , 187 – 191 .
   Google Scholar
• Gupta , R. ; Jain , A. ; Jain , M. ; Joshi , R. One-pot synthesis of 2-amino-3-cyano-4,6-diarylpyridines under ultrasonic irradiation and grindstone technology . Bull. Korean Chem. Soc. 2010 , 31 , 3180 – 31282 .
   Web of Science ®Google Scholar
• Altalbawy , F. M. A. Synthesis and antimicrobial evaluation of some novel bis-α,β-unsaturated ketones, nicotinonitrile, 1,2-dihydropyridine-3-carbonitrile, fused thieno[2,3-b] pyridine, and pyrazolo[3,4-b]pyridine derivatives . Int. J. Mol. Sci. 2013 , 14 , 2967 – 2979 .
   PubMed Web of Science ®Google Scholar
• Purushothaman , M. ; Loganathan , K. ; Shithick , A. K. Synthesis, characterization, and biological importance of aminocyanopyridines . Int. J. Chem. Tech. Res. 2012 , 4 , 479 – 483 .
   Google Scholar
• Sarda , S. R. ; Kale , J. D. ; Wasmatkar , S. K. ; Kadam , V. S. ; Ingole , P. G. ; Jadhav , W. N. ; Pawar , R. P. An efficient protocol for the synthesis of 2-amino-4,6-diphenylpyridine-3-carbonitrile using ionic liquid ethylammonium nitrate . Mol. Divers. 2009 , 13 , 545 – 549 .
   PubMed Web of Science ®Google Scholar
• Kidwai , M. ; Thakur , R. ; Rastogi , S. Ecofriendly synthesis of substituted pyridine and pyrido[2,3-d]pyrimidine derivatives . Russ. Chem. Bull., Int. Ed. 2005 , 54 , 1523 – 1526 .
   Web of Science ®Google Scholar
• DeGraw , J. I. ; Tagawa , H. An alternate synthesis of 6-substituted 5-deazapteridines . J. Heterocycl. Chem. 1982 , 19 , 1461 – 1463 .
   Web of Science ®Google Scholar
• Taylor , E. C. ; Dumas , D. J. Pteridines 48: Utilization of 3,3-dimethoxy-2-pyrolidinopropene for the synthesis of folic acid, N2′-acetyl-7-folic acid, and 5-deaza-7-folic acid . J. Org. Chem. 1981 , 46 , 1394 – 1402 .
   Web of Science ®Google Scholar
• Paronikyane , G. ; Sirakanyan , S. N. ; Noravyan , A. S. Synthesis of derivatives of pyrido[2,3-d]pyrimidines condenced with tetrahydropyran and tetrahydrothiopyran . Chem. Heterocycl. 1993 , 29 , 1454 – 1457 .
   Google Scholar
• Marco , J. L. ; de los Rios , C. ; Carreiras , M. C. ; Banos , J. E. ; Badia , A. ; Vivas , N. N. Synthesis and acetocholinesterase/butyrycholinesterase inhibition activity of new tacrine-like analogues . Bioorg. Med. Chem. 2001 , 9 , 727 – 732 .
   PubMed Web of Science ®Google Scholar
• da Silva , D. B. ; Samadi , A. ; Infantes , L. ; Carreiras , M. ; do , C. ; Marco-Contelles , J. Synthesis of (E)-diethyl-6,6′-(diazene-1,2-diyl)bis(5-cyano-2-methyl-4-phenylnicotinates) a new type 2,2′-azopyridine dyes . Tetrahedron Lett. 2010 , 51 , 6278 – 6281 .
   Web of Science ®Google Scholar
• Verĉek , B. ; Leban , I. ; Stanovnik , B. ; Tisler , M. Neighboring group interaction in ortho-substituted heterocycles, 2: 1,2,4-Oxadiazolylpyridines and pyrido[2,3-d]pyrimidine-3-oxides . J. Org. Chem. 1979 , 44 , 1695 – 1699 .
   Web of Science ®Google Scholar